


There's A High Chance You'll Like Him

by xmzame



Category: Supernatural
Genre: Alternate Universe, Awkward Conversations, Awkward Flirting, M/M, Parent-Teacher Conference, Previous One-Night Stand, teacher!Castiel
Language: English
Status: Completed
Published: 2016-01-05
Updated: 2016-01-05
Packaged: 2018-05-11 23:39:25
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,724
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5645983
Author URL: https://archiveofourown.org/users/xmzame/pseuds/xmzame
Summary: <blockquote class="userstuff">
              <p>AU: Dean attends a Parent-Teacher conference to represent Sam's parent, and sees the freakishly familiar face of Sam's English teacher, Mr Milton.</p>
            </blockquote>





	There's A High Chance You'll Like Him

**Author's Note:**

> Before reading this fic, please know that I'm not entirely sure of how Parent-Teacher conferences work in America, so I kind of winged it. I'm sorry for any errors!

_For Sam’s sake_ , Dean reminded himself.

He’d only visited three of Sam’s teachers one-to-one so far and he was already bored out of his mind. He shouldn’t even be the one representing Sam’s parent, but there was no way of convincing or properly talking to John to get him to go to this conference thing.

_“Please, Dean, teachers have been bugging me my whole life about it, and it’s my final year.”_

Sam’s voice rang in his head as he forced a last smile at the History teacher he just spoke to, before stepping away from the table. He could feel the guy’s eyes judging him as he walked away.

Dean took a deep breath. “Keep it cool, Dean. Keep it cool,” he muttered to himself. He scanned the list of teachers on the paper he was given and looked for anymore of Sam’s teachers that was in the library.

 _Mr Milton_. He was Sam’s English teacher, according to the separate list Sam gave him.

 ** _There’s a high chance you’ll like him,_** Sam wrote next to the name.

Dean rolled his eyes. It was probably the best note Sam gave him, after having to deal with **_Mr MacLeod – Sorry Dean. Be patient with him._**

He surveyed the library half-filled with teachers, looking at the names placed on each table for a Mr Milton. His eyes finally caught the name as he approached closer to the organized desk with an empty-seated chair. Bathroom break, probably.

Dean sighed and turned away as he looked back to the teachers’ list. There wasn’t anybody else in the library he hadn’t seen yet, so he figured he was going to the hall to see **_Ms Lilith – She hates and loves me at the same time, be aware._**

That didn’t sound so good. If only he could find some excuse to skip the rest of this whole thing—

“Were you here to see me?” a voice asked behind him. “I’m so sorry, I had to take an important call.”

Dean turned around, assuming the person was talking to him. The guy stood behind Mr Milton’s desk with a polite smile in greeting.

“Oh, yes I was,” Dean uttered, checking the list again to see if it was English. He shook the hand Mr Milton held up for him before finally looking him in the eye. Dean nearly paused at how the shake suddenly slowed down, and realized Mr Milton was staring at him in complete shock.

Dean was freaked out by how familiar he looked, but he couldn’t quite place it yet. Mr Milton awkwardly released his hand and stood there with his mouth hanging open.

“…Dean?”

Slowly, the more Dean took in his looks, he finally registered where he’d seen Mr Milton before. Mr Milton didn’t wear thick-framed glasses the night he met Dean. Oh God, it was only two weeks ago and Dean had already forgotten his first name.

“Oh crap,” Dean whispered to himself. He cleared his throat and looked around to see if anyone in the library noticed the awkward tension between them, but they seemed occupied anyway.

“Um- sit. Please,” Mr Milton finally spoke as he took his own seat.

Dean did the same, awkwardly smiling at him. “I’m uh, Sam Winchester’s brother. Here to um, talk about him, I guess.” He glanced down at his hands nervously. “So what can you tell me…Mr Milton?”

Mr Milton stared at him with an almost annoyed expression. “Castiel. In case you forgot,” he said sternly and shuffled through a few documents in his hands.

 _Castiel_. _Castiel. Casti-fucking-el._ Dean felt like slapping his own forehead repeatedly and burying himself ten feet under. How could he forget a name so easily?

“Castiel, right. God, I’m so- usually I’d have the courtesy to remember someone’s name, I swear. You know what, I won’t bother you anymore, I’ll just go—” Dean was about to get out of his chair.

“Stay.” Castiel made it clear enough with the tone of his voice, and Dean immediately obeyed, holding onto the seat tightly. Castiel sighed. “Winchester. I should have figured,” he muttered, shaking his head as he looked at one of Sam’s assignments.

Dean made an attempt to smile at him, but only received the unchanged expression on Castiel’s face. “I guess I should have asked which school you worked at,” Dean replied with a nervous laugh.

“That would’ve been none of your business,” Castiel simply said.

Castiel was making this so damn hard. Dean’s mind went back to two weeks ago.

It was just a one-night stand. A really, _really_ great one-night stand, in which they both agreed that they wouldn’t have to see each other again. Yet there they were, caught in the middle of the most awkward situation Dean had ever dealt with, in a _library_.

“Um, Castiel- if I can call you that still, I think it’d be a whole lot easier if we didn’t make this awkward,” Dean said. He cleared his throat again. “Please?”

Castiel continued staring at him for a few seconds and finally nodded with a short sigh. “Of course,” he agreed, pushing the rim of his glasses to the bridge of his nose. “I’m sorry, that was highly unprofessional of me. So, Sam Winchester. One of the top students.”

Dean eventually released the awkward air floating between them with a genuine smile. “Yeah, that sounds like him.”

“He doesn’t seem to have any problems with his homework,” Castiel remarked as he checked a whole list of names with a bunch of ticks done neatly in a table. “Always on time. And his writing is magnificent for someone his age.”

“Yeah, the kid reads a lot,” Dean mentioned. “He says he wants to write a book someday, actually.”

Castiel smiled at that. It was nice to finally see that for a change.

“Oh. That’s wonderful to know. I hope he does,” Castiel said.

Dean nodded back, waiting for any other comment about his brother.

“His attendance, though…” Castiel pointed out. “It’s not any of my business, but he misses class more than once a week sometimes. Is there anything I should be worried about?”

Dean would have said, _Yeah, that’s kinda what happens when you have an absent dad most of the time._ “Uh, everything’s okay. Nothing to worry about. As long as Sam gets his work done and learns enough, right?”

Castiel studied him for a bit. “Right. But if there is anything going on, I’d be glad to give him an extension of time to finish his work. I don’t want any of my students to be too stressed.”

Dean’s heart did a soft flutter when Castiel stared at him longer. “Thanks. I’m sure he’ll let you know if he needs it.”

“Alright. So Dean, I don’t think it’d be necessary for me to bore you with the English syllabus,” Castiel notified.

Dean sighed of relief. “Thank _God,_ ” he uttered. He realized how rude that probably sounded and started to correct himself. “I mean- no, please. Tell me how English works.”

Castiel grinned. “It’s alright. I’m sure you know enough.”

“So uh, are we done talking about Sam?” Dean asked quietly.

“I suppose. That might have been the shortest one-to-one conference I’ve ever had,” Castiel claimed, looking at his watch.

Dean bit the bottom of his lip to suppress a smile. “Then would it be okay if I requested for _another_ one-to-one conference with you?”

Castiel softly smiled at him. “Would we still be talking about Sam?”

“I was thinking other things,” Dean murmured, smirking.

Castiel pondered on it, wandering his eyes away. “I’ll have to think about it.”

Dean sighed. “Look, I’m sorry I forgot your name. I really am. I’m not the type of guy who does that.”

“Then, are you the type of guy who easily loses a phone number?” Castiel asked, slowly reaching out for a card on the table.

“I hope not,” Dean related, pouting out his lip. “That’d be a pretty huge loss for me.”

Castiel simply stared at the card with his number on it and showed it to Dean. “How much do you actually want this?”

“I don’t know how much. But you seem like a great guy. I left early that morning, so I didn’t get to tell you— it was fun, what we did. I mean I’m not saying I wanna do it again. Wait,-”

Dean halted in his speech when Castiel offered him the card with his number on it.

“Call me for coffee. Or dinner. Both, maybe.”

Dean beamed as he gently took the card out of Castiel’s hand. “I will. Thanks, Castiel.”

“Cas. It’s easier to remember,” Castiel teased.

“I won’t forget your name!”

Castiel looked behind Dean and sheepishly smiled at whoever was behind him. “I’d hate to send you away, Dean, but the whole conference is almost coming to an end, and some parents have me scheduled.”

“Right, so I’ll…” Dean stood up from his seat and offered his hand to shake, shyly smiling. The couple behind him drew closer. He cleared his throat and said, “I’ll definitely call you for another chat, Mr Milton.”

Castiel beamed. “Looking forward to it.”

Dean sent him a wink and managed to catch Castiel blushing before he walked away. He left the library to go see some other teachers, _for Sam’s sake_ , Dean reminded himself again. Dean practically slept with his eyes open throughout the whole thing, nodding at the right time and asking the simple questions.

Thirty minutes later, the conference came to an end and Dean was home in no time, staring at the number on Castiel’s card.

“Hey, how was it?”

Dean quickly looked up and hid the card away, smiling at Sam without realizing. “Ah, you know. Conferences. Everybody loves you, Sam.”

Sam furrowed his eyebrows. “What are you all smiley about?”

“Nothing. I’m just glad you’re doing really well in school,” Dean said as he walked past him, ruffling his brother’s hair into a mess.

Sam grunted, “Stop doing that! Seriously, how did it go?”

Dean tried to stop smiling. “Let’s just say, you were right about Mr Milton. There’s a _very_ high chance that I like him.”

“Oh God, I didn’t mean it like that,” Sam whined.

“Too late, Sammy!” Dean chided across the room and raised an arm, flicking Castiel’s card in the air.


End file.
